


Drag Queens,  Fancy Drinks and Glitter

by curious_sherlockitten



Category: Supernatural
Genre: Drag Queens, First Kiss, Fluff and Angst, M/M
Language: English
Status: In-Progress
Published: 2015-06-07
Updated: 2017-05-25
Packaged: 2018-04-03 09:11:40
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 3,162
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4095268
Author URL: https://archiveofourown.org/users/curious_sherlockitten/pseuds/curious_sherlockitten
Summary: <blockquote class="userstuff">
              <p>When Dean accidentally wanders into a gay bar, he doesn't expect to meet the woman of his dreams.</p>
            </blockquote>





	1. Chapter 1

7:35 pm  
Dean checked his watch for the third time in fifteen minutes. 'you have got to be kidding me..'  he twisted his mouth into the closest thing to a smile that he could manage, nodding absently at his date who had been in the midst of telling him a story about...   Something or other. Dean hadn't been paying attention.

  
When his father had pulled him into his office on Monday, the last thing that he had suspected the surprise meeting to be about was to discuss a possible date between himself and Becky Rosen, daughter of the owner of one of Winchester LTD's most faithful business partnerships,  and John Winchester's old friend. Of course 'possible' was just formality. John expected his son to follow through on the plan if he knew what was best.

  
Dean  agreed to the arrangement, not beacause of genuine interest in Becky, who seemed more interested in his brother Sam anyways, but because he knew that he didnt actualy have an option. Anyways, how hard could it be to spend one evening with the woman?

  
They arrived at the restaurant at 7:00 and were served immediately, having pre ordered. The two had met several times before at charity banquets and open houses, so since they weren't complete strangers, the dinner hadn't been as awkward as it could have been. Though to go as far as saying that the evening had been a successful one was unlikely.

After getting through the initial pleasantries, Dean had tried to strike up a conversation, any conversation, but was shot down each and every time by Becky trying to change the subject to Sam, or Fanfiction, what ever that was. Eventually, he settled in to hear about one of the many online stories that she was working on.

7:40

'Is my watch right?' Dean wondered, frowning. 'How have we only been here forty-'  
"-Dean?" He looked up at his date "huh? I mean I'm sorry I must have zoned out.." he tried to apologise but it came out with more of a wistful  tone instead.  
"Well I was just wondering what your opinions are about the Shurley deal. That's all daddy can talk about now a days."  
"Oh, well- of course it will bring in more business and facilitate our companies' trade deals out east, so on that front I am certainly pleased that the final papers have been agreed on.They're actually going to sign them this coming Monday at the bord meeting."

Dean tried to sound cheerful about it, he really did, but having been in charge of the project, he was bored to death by the subject. It had taken up all of his time for months.  
Dean was just glad that it was done. Though he knew that there would be a new five projects dumped on him before he had time to savour his freedom.

At 9:30, after they had finished their meals, Becky demanded that they simply must try the caramel liqueur  cheesecake. He was given the next day off work but told her that he should be heading home because the next morning would be an early one.

Dean was glad to drop her off and then head out to his favorite bar 'The Road House'. He'd been going there for several years and they had the best mixed drinks he's found. Dean's weakness was the sweet tast of an appletini or a blue Hawaiian (well that and a good pie) , a fact that his brother teased him endlessly about.

Dean settled into a bar stool and flagged down the bar tender.  
"One vodka cain please" he called.  
Out, reading the specialty drinks list.

After several rounds, a pleasantly buzzed Dean reached into his jacket pocket for his phone and dialed Sam's number.  When he didn't pick up on the first... five calls, he tried again.  
On the 10th call there was finally an anwser,

"Dean it's date night with Gabriel, you know this." 

"Well yes but I'm much more fun than your weirdo of a boyfriend.."

"Um Dean,  you're currently on speaker phone" 

"you pain me so, Dean" Gabriel's snarky voice flooded his ears through the phone.

"AH. ..Gabriel...youuuu-"

"Dean how drunk are you?" The couple asked simultaneously. Sam finishing with his trade mark sigh that presented both his annoyance and pity in one exhale.

Dean was about to anwser when music started playing over some speakers behind him. He turned around and his eyes rested on a large stage, decorated with tassels and Glitter.

" Since when does The Road House have a stage?" He thought out loud.

"Road House? This isn't The Road House, this is heaven!" The bartender shouted over the music.

A confused Dean stared awkwardly at the stage until a scantily dressed woman stepped out onto it. Her hair was waved and swept to the side,framing her face. Forgetting his call with Sam, he tucked his phone in his pocket and wound through the crowd forming around the stage. The woman looked up and Dean felt pinned in place by her pale blue eyes.

She was beautiful.

**Notes for the Chapter:**

> Thanks you so much for reading and I hope you enjoyed chapter one! I'm in the midst of writing an other and will post it as soon as possible :)  
> Comments and feedback are loved and appreciated!


	2. Chapter 2

'As the music died down, the woman who had begun to speak to the crowd, which was growing by the second, transfixed Dean.

"How are we tonight my angels?" Her slightly raspy voice sent shivers down Dean’s spine and earned an enthusiastic "whoop" from the excited audience. She laughed, "I've got something special prepared for you tonight babies!" Winking, Dean could have sworn it was directed at him, she twirled around to face the back of the stage, striking a pose as a new song started.

_'Take a look around the room, love comes wearing disguises-'_

With the first line, the woman slowly looked over her shoulder and turned, swiveling her hips as she went.

_'I'm a man who's got very specific taste._

_You're just my type,  oh, you got a pulse and you are breathing'_

Dean was amazed and in awe of her as her dancing managed to be both graceful and erotic in a way that had Dean completely worked up by the end of the number. With a parting remark, she left the stage to a chorus of people chanting something that he couldn’t quite make out, but what Dean assumed was her name.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Dean sat on the bar stool nursing his (how many drinks has it been?) cocktail. He couldn’t get the image of the dancing woman out of his head, ignoring the looks he was getting from the other cliental, mostly men, which should have tipped him off that this was not his usual type of bar.

“Can I get you anything sweetie?” The bartender raised an eyebrow. Downing the rest of the drink in front of him, Dean set his glass down and slid it towards the man.

“Another of what ever _that_ was,” Dean eyed the man’s nametag, “Chuck” he added, his eyes crinkling as he smiled.

“Sure thing hon’ ” Chuck winked and got to work fixing up the drink.

Dean turned around and leaned against the bar, surveying the room. Lining the walls was a variety of faux leather seating, some sections given a slight bit of privacy by Asian inspired room dividers. In the middle of the room was a large dance floor, crowded with men.

“Here you are.” Dean was shaken back to alertness by Chuck's kind voice.

“ah. Thaaank you kind sir.” He smirked, taking a sip from his glass. Dean turned back towards the dance floor to do more people watching- right into a rather scruffy man wearing a worn ball cap that didn’t seem to match the rest of his outfit, and spilled his drink.

“Watch it ya idjit..” the man grumbled.

“damn it..” Dean set the glass back down, frowning.

“you ok bobby?” Chuck asked the older man, who was a regular by the familiar way chuck addressed him.

“ya ya…” the man, Bobby, waved off the cloth that Chuck offered.

“Will you be wanting an other one of those?” he gestured to the empty cocktail glass.

“Eh, no thank you chucky, is it cool if I call you that? I’ve probably hit my limit anyways” dean laughed and started to make his way, only going off course twice, because of drunken stumbling, to the men’s room.

There were two doors, only two, but dean had a hard time figuring out which led to the bathroom. After staring at them for a good 5 minutes, he finally did eeny-meeny-minie-mo and picked a door to try.

Slamming the door behind him, the blond leaned heavily against it, forehead pressed into the wood. A small gasp sounded behind him and Dean turned, finding himself face to face with the dancing woman from before.

“Excuse me sweetheart but this is my dressing room.” The woman looked at him expectantly and dean realized she was waiting for him to respond or leave. And he definitely didn’t want to leave.

“I-I’m sorry miss” He smiled crookedly and leaned in as if sharing a secret, “I was just lookin for the little boys room.”

The woman studied his face and smiled, “you’re completely hammered aren’t you?” she asked crudely, chuckling.

“Well it would seem that way wouldn’t it?” dean held out his hand “the names dean” he grinned.

“She eyed his hand for a moment before taking it. “Chastity”

“Lovely name” He ran his thumb over the back of her hand. “Whats a lovely lady such as yourself doing in this sort of place” he asked, winking dramatically.

Chastity let out a full laugh at this. “Wow, well Dean, you really must be drunk, but still charming aren’t you?” she let go of his hand. “Ill be done is here in a minute, join me at my table out there?” she gestured towards the main room.

“Well how could I say no to that?” dean grinned crookedly again, winked, and slipped back through the door.

“Well, well ,well” Chastity smiled to herself.

 

 

**Notes for the Chapter:**

> Thank you guys for reading! Also, thanks for the kudos on the last chapter, its nice to know that someones actually reading this darn thing! haha :P  
> I'll post the next chapter as soon as possible, but finals are looming so i can't make any promises on when that will be.  
> AND a GINORMOUS thank you to my friend Amelia who came up with Cas' Drag name :) i owe you big! (for those who don't know, its a reference to the girl in the brothel that Dean takes Cas to in 5x03)  
> p.s. ~ The song that Cas lip synched to in this chapter was 'My Type' by Saint Motel


	3. Chapter 3

**Notes for the Chapter:**

> Another chapter! Wow the third one this week? I'm sort of on a writing spree haha!

Dean waited impatiently in an uncomfortable leather love seat. He had to shift every so often or the left side of his ass would fall asleep. Though mind was still blurred from the alcohol but there was no mistaking when the woman, Chastity, had asked him to join her. He had known from the moment he saw her that he had to speak to her. In all the bars, dives and charity events that he's attended, no one had ever captured his attention  like she had. 

 "Hey there sweetheart" her sweet low voice went directly south from Dean's ears. "I thought you'd left, without a second peek" she winked and sat in the chair next to Dean's. 

 "Leave with out seeing you again?"Dean faked a gasp. "Crazy town!" 

"Crazy town? What's that supposed to be?" She teased, leaning foreword and smirking.

"It's an expression ok?" Dean pouted.

Tilting her head back and laughing, Chastity eyed him up again. 

 "I was going to suggest a drink but I think you've already had YOUR last."

 "You maaaay have a point" he shows off a toothy grin.

 " so, Dean, what brings you here tonight? Drowning your sorrows like the rest of us?" She joked.

 Dean's grin faltered. " ya.."  he looked down "you could say that."       

 "Hey" Chastity reached her arm across

 The table between them and rested her palm on the back of Dean's hand. "You alright sweet heart?" 

"Not exactly" Dean shook his head, his voice drifted off. "you don't want to hear about my shitty issues" he was tempted to pull his hand away, but left it where it was, enjoying the heat, the feel of their proximity comforting him.

"Sweetie, we all have our issues, god knows I do, so spill."

Sucking in a deep breath, Dean thought about where to start.

"I'll tell you about my crappy life if you tell me about yours." He offered.

They spent the rest of the evening...night... like that, Dean recounting stories of his hard ass father who cared more about his work and advancing the family company than his two young sons, who lost their mother in a freak house fire when they were young. His need to obey and impress his father for some sort of recognition growing up with him.    

Chastity told him of her absent father. They had no family to speak of that he could push her and her brother onto, and so they were sent to a boarding school for the entirety of her academic career.

It wasn't till they noticed the club clearing out that they realized that they had been talking for hours.

"Well mister, I ought to get you a cab! I'm certainly not letting you drive home tonight so don't even think about it." She gave Dean a stern look.

"Yoou are such a kind lady" he pointed at her using two fingers.

Chastity shook her head and chuckled. "And yoouu are still hammered aren't you?" Dean just smiled in response.

"Okay, come on, cab is on me. She dragged him out of the bar and tucked him into a waiting cab, handing some money to the driver. "Get home safe, you silly man" she patted his arm, winking.

"Chastity, you are an amazing woman."  Dean cooed. The woman just grinned as if at a joke. "What's so funny??" He asked, wondering what joke he had missed.

"Just that you keep calling me an amazing WOMAN." She grinned, slamming the cab door.

"Well that's what you are!" Dean was confused by the conversation, but told the driver his address and slumped into his seat.

Dean's apartment was in the center of the city in one of its newer buildings. It cost a fair bit, But man was the view worth it. Not that Dean noticed it much when he got home. 

As soon as dean got through the door he almost passed out. He barely managed to take off his shoes before crawling into bed, clothes and all.

~~~~~~~~~~~~~~~~~~~~

The next morning, Dean woke with a splitting head ache. His alarm was loud and felt like daggers to his ears. He groaned and stretched out an arm towards the sound, slamming his hand down on the snooze button. 

" Shut. Up. " Dean rolled onto his face and pulled his pillow over his head. 

The second time he woke up, he knew that he couldn't ignore the world any longer.  Rolling onto his back, he stared up at the ceiling fan.

"Shit." His head hurt worse than he remembered. Hauling himself up and out of bed was hard work, but thoughts of his espresso maker that waited in the kitchen was good incentive. 

Dean prepared his coffee and pulled out his favorite coffee mug, the one adorned with a picture of a 67 Chevy Impala, setting it on the counter next to the answering machine. There were two messages waiting. One from Becky, Saying a simple thanks for the dinner the night before, which he quickly deleted. There was also one from his brother, inviting him for brunch with him, his boyfriend Gabriel, and a few of their friends, including Gabriel's brother who Sam had been telling him he'd get along with famously for ages.

Dean looked at the clock on the stove, if he got ready just then he would have enough time to make it to their house for free food. If it was anyone else offering Dean would have declined, but Sam had snagged himself a chef of a boyfriend. His stomach rumbled and he glanced at the clock again. 

"Aw, what the hell." Dean sent a quick text to Sam,  took another sip of his coffee and headed to his room to change and give his hair a quick brush through.

 

**Notes for the Chapter:**

> Thanks for reading! Comments are loved and appreciated!!!  
> If you have any ideas or requests then send them my way, anything that helps me to improve the fic for you guys is loved :)


	4. Chapter 4

**Notes for the Chapter:**

> The forth chapter... finaly.  
> I've had half of this chapter written for ages and thought it was time to finish it!

The ride to Sam and Gabriel's place took a bit longer than usual. The sun was out, making it a perfect day to be outside and a parade down one of the main roads caused him to have to take a detour route. 

Dean's stomach rumbled Continuously throughout the whole ride and he cursed himself for not at least grabbing a granola bar to eat before he left.

He had to park on the road when he arrived because the driveway was full. Parked beside Sam's bright green smart car was a silver Toyota Yaris. 'Oh no. What kind of pansy do they have over this time' Dean scowled. This was going to be a long brunch.

The last time his brother had invited him over for brunch, he had been bombarded with yammering and pleasantries from an over friendly Garth. He was one of Sam's work friends and more closely resembled a lost puppy than a human. The man was apparently a star employee at "Charlie's ", the youth center that he and Sam worked at.

Dean crossed his fingers behind his back for more tolerable company this time around as he rang the door bell.

"Deano!" Gabriel pulled Dean in for a bear hug, clamping his arms down so he couldn't escape. 

"Hello Gabriel" Dean choked out in response, arms hanging limply at his sides. After finaly being released from the hug prison, he was ushered through the bright house and out onto the deck. Flowerpots decorated the perimeter, and there was a large table in the center.  It was full of Gabriel's famous danishes and crepes, along with countless toppings and several types of fruit salad. Dean's inner monologue cheered excitedly as he eyed the fresh baked goods. Then his eyes were drawn to another sight... A familiar looking young man who was nibbling at a bran muffin.

"Stop ogling Dean, I know he's cute but at least introduce yourself first." Gabriel winked.

Dean blinked. "Do I know you?"

The young man opened his mouth to respond but was interupted my Sam. "Dean, this is Castiel, Gabriel's brother and a good friend of mine. Cas, this is my brother Dean" Sam smiled and ushered Dean into he seat next to Castiel.

"Hello Castiel" Dean half grinned, not expecting much from a friend of Sam's. 

"Please, call me Cas." He winked at Dean. "Nice to 'meet' you Dean." 

The rest of the brunch went by fast, with Dean spending most of his time chatting with Cas. When it was time to leave Dean collected his jacket and said his good byes. He could feel a pair of eyes on him as he walked to his car.

He stuck his hands in his pockets, searching for the keys, but instead found a small slip of paper, carefully folded with a heart drawn on the front. Curious, Dean unfolded it to find a phone number written in neat hand writing and signed with a "C". 

 _Chastity_... 

Dean pocketed the number with a smile on his face. _So she does wast me to call her_.  __He didn't notice that the edge of the paper had the same pattern as the napkins that had been layed out with brunch.

**Notes for the Chapter:**

> Thanks for reading friends! As usual, comments and questions and loved and encouraged♡  
> I'm going to start adding chapters to this fic again regularly (Hopefully)!


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